isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate
• 英文别名: isopropyl 3,7,11-trimethyl-2,4E,10-dodecatrienoate；trans Isopropyl 3,7,11-trimethyldodeca 2,4,10-trienoate；propan-2-yl (4E)-3,7,11-trimethyldodeca-2,4,10-trienoate
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: PXQZZXXYQJDJPE-NLFVLIHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate 在 ice 、 正己烷 、 水 、 calcium sulfate 作用下， 反应 49.25h， 以to yield trans isopropyl 11-chloro-3,7,11-trimethyldodeca-2,4-dienoate的产率得到trans Isopropyl 11-chloro-3,7,11-trimethyldodeca-2,4-dienoate
  参考文献：
  名称：

  Alkoxy substituted aliphatic di-olefinic halides

  摘要：

  脂肪族烃三烯和取代脂肪族双烯卤化物及其衍生物，其中间体，其合成以及昆虫控制。

  公开号：

  US03970704A1
• 作为产物：
  描述：

  4-hydroxy-6,10-dimethylundec-9-en-2-one 在 对甲苯磺酸 、 sodium sulfate 作用下， 以 乙醚 、 苯 为溶剂， 反应 5.0h， 生成 isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate
  参考文献：
  名称：

  Synthesis ofS-(+)-methoprene

  摘要：

  An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. approximately 50%) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol. This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5). Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one. The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14% overall yield.

  DOI：

  10.1007/bf00699984

文献信息

• Odinokov, V. N.; Kukovinets, O. S.; Zainullin, R. A., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 4.1, p. 650 - 653
  作者：Odinokov, V. N.、Kukovinets, O. S.、Zainullin, R. A.、Tolstikov, G. A.

  DOI：——

  日期：——
• Synthesis ofS-(+)-methoprene
  作者：V. N. Odinokov、G. Yu. Ishmuratov、R. Ya. Kharisov、E. P. Serebryakov、G. A. Tolstikov

  DOI：10.1007/bf00699984

  日期：1993.1

  An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. approximately 50%) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol. This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5). Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one. The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14% overall yield.
• Alkoxy substituted aliphatic di-olefinic halides
  申请人：Zoecon Corporation

  公开号：US03970704A1

  公开（公告）日：1976-07-20

  Aliphatic hydrocarbon tri-olefinic and substituted aliphatic di-olefinic halides, and derivatives thereof, intermediates therefor, syntheses thereof, and the control of insects.

  脂肪族烃三烯和取代脂肪族双烯卤化物及其衍生物，其中间体，其合成以及昆虫控制。